Construction of chemoenzymatic cascade reactions for bridging chemocatalysis and Biocatalysis: Principles, strategies and prospective

Liu, Yunting; Liu, Pengbo; Gao, Shiqi; Wang, Zihan; Luan, Pengqian; González‐Sabín, Javier; Jiang, Yanjun

doi:10.1016/j.cej.2020.127659

Cited by 75 publications

(66 citation statements)

References 103 publications

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“…Whether a sequence calls for a reagent from the 'chemo-' or 'bio-' toolbox matters not; both are on the shelf; both do their jobs, added consecutively and interchangeably into the same reaction medium: water. 62,63 Such enabling technologies satisfy what Hayashi has been promoting, albeit in organic media, for years: 'pot' 64 and 'time' 65 economy.…”

Section: Account Synlettmentioning

confidence: 98%

“…66 And many more combinations featuring 4-5 sequential reactions with different chemo-catalysis reagents together, in water, with various enzymes (e.g., ene-reductases, lipases, and transaminases) are coming, in varying orders of appearance within each scheme. 62,63,67 Remarkably, the presence of a surfactant may also discourage enzymatic inhibition by providing, in micellar form, a 'reservoir' effect whereby the lipophilic product can be re-localized, drawn away from buildup in and around the enzymatic pocket. The same aqueous nanomicellar medium also provides a location for chemo-catalysts to reside, thereby decreasing their potential denaturing effect to-…”

Section: Account Synlettmentioning

confidence: 99%

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Illuminating a Path4914. Copyright 2016 Wiley for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

Lipshutz¹

2021

Synlett

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A personalized account is presented describing some of the stories behind the scenes in efforts to convert organic chemistry into a more sustainable discipline. These are part of a group ‘crusade’ started almost 15 years ago aimed at providing technologies illustrative of how key reactions used today can be ‘faster, better, cheaper’ when run in recyclable water. Hence, the option now exists to do organic synthesis in a far more environmentally responsible fashion. By contrast, most of organic chemistry developed over the past 200 years that relies on organic solvents continues to generate enormous amounts of pollution, while depleting finite petroleum reserves and our supplies of many precious and base metals. Making the switch to water, Nature’s chosen reaction medium, akin to that in which bio-catalysis is typically performed, is inevitable.1 The Story Begins: A Different Type of Prejudice2 Are We up to the Challenge? Too Late Now…3 ‘Impossible’ Reactive Metal Chemistry in Water4 Didn’t I Once Say: ‘It’s All about the Ligand’?5 What Happens When Our Supply of Palladium Runs Out?6 What Are the Implications from These Tales for Today and Tomorrow?7 What Is the ‘Broader Impact’ of This Work?8 The Bottom Line…

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Section: Account Synlettmentioning

confidence: 98%

Section: Account Synlettmentioning

confidence: 99%

Illuminating a Path4914. Copyright 2016 Wiley for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

Lipshutz¹

2021

Synlett

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“…The attractiveness of the “enzymatic one-pot reaction” concept is the most interesting inspiration from nature for pharmaceutical and fine chemical production. The development of valuable biocompounds by microorganisms as biocatalysts is the much awaited goal of synthetic chemistry ( Liu et al, 2020 ). The biotransformation processes mediated by endophytic fungi as enzymes or as whole-cell catalysis result into new pharmaceutically active molecules.…”

Section: Applications Of Endophytic Fungi As Biocatalystmentioning

confidence: 99%

Endophytic Fungi-Mediated Biocatalysis and Biotransformations Paving the Way Toward Green Chemistry

Choudhary

Gupta

Dhar

et al. 2021

Front. Bioeng. Biotechnol.

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Catalysis is a process carried out in the presence of a heterogenous catalyst for accelerating the rate of a chemical reaction. It plays a pivotal role in transition from take, make, and dispose technology to sustainable technology via chemo- and biocatalytic processes. However, chemocatalyzed reactions are usually associated with copious amounts of perilous/hazardous environmental footprints. Therefore, whole-cell biotransformations or enzyme cocktails serve as cleaner biocatalytic alternatives in replacing the classical chemical procedures. These benchmark bioconversion reactions serve as important key technology in achieving the goals of green chemistry by eliminating waste generation at source. For this, nature has always been a driving force in fuelling natural product discovery and related applications. The fungal endophytic community, in particular, has undergone co-evolution with their host plant and has emerged as a powerful tool of genetic diversity. They can serve as a treasure trove of biocatalysts, catalyzing organic transformations of a wide range of substances into enantiopure compounds with biotechnological relevance. Additionally, the biocatalytic potential of endophytic fungi as whole-intact organisms/isolated enzyme systems has been greatly expanded beyond the existing boundaries with the advancement in high-throughput screening, molecular biology techniques, metabolic engineering, and protein engineering. Therefore, the present review illustrates the promising applications of endophytic fungi as biocatalysts for the synthesis of new structural analogs and pharmaceutical intermediates and refinement of existing proteins for novel chemistries.

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“…The advantages of this strategy are considerable (i.e., product purification, cost, time and effort saving) in comparison to traditional multi-step synthetic procedures. The application of metal-, organo-or bio-catalysis have played a role in developing this type of strategy, whereas, the multi-catalytic approach based on the concurrent activity of different catalysts is a less exploited concept due to possible incompatibilities between the different catalytic systems used [52,53]. The metal/lipase co-catalyzed DKR is a successful example of this type of approach.…”

Section: Cascade Synthesis Of Complex Molecules Including Dkrmentioning

confidence: 99%

Progress on the Stereoselective Synthesis of Chiral Molecules Based on Metal-Catalyzed Dynamic Kinetic Resolution of Alcohols with Lipases

Ferraccioli¹

2021

Symmetry

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Metal/lipase-combo catalyzed dynamic kinetic resolution (DKR) of racemic chiral alcohols is a general and practical process to obtain the corresponding enantiopure esters R with quantitative conversion. The use of known Ru-catalysts as well as newly developed homogeneous and heterogeneous metal catalysts (Fe, V) contributed to make the DKR process more sustainable and to expand the substrate scope of the reaction. In addition to classical substrates, challenging allylic alcohols, tertiary alcohols, C1-and C2-symmetric biaryl diols turned out to be competent substrates. Synthetic utility further emerged from the integration of this methodology into cascade reactions leading to linear/cyclic chiral molecules with high ee through the formation of multiple bonds, in a one-pot procedure.

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Construction of chemoenzymatic cascade reactions for bridging chemocatalysis and Biocatalysis: Principles, strategies and prospective

Cited by 75 publications

References 103 publications

Illuminating a Path4914. Copyright 2016 Wiley for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

Illuminating a Path4914. Copyright 2016 Wiley for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

Endophytic Fungi-Mediated Biocatalysis and Biotransformations Paving the Way Toward Green Chemistry

Progress on the Stereoselective Synthesis of Chiral Molecules Based on Metal-Catalyzed Dynamic Kinetic Resolution of Alcohols with Lipases

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